2-Amino-6-benzothiazolol → 2-(4-Nitrophenyl)imidazo[2,1-b]benzothiazol-7-ol

HRID 333718Notes

Reaction equation

HRID 333718 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH:12]1[C:17]([C:18]([CH2:20]Br)=O)=[CH:16][CH:15]=[C:14]([N+:22]([O-:24])=[O:23])[CH:13]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)C>[N+:22]([C:14]1[CH:15]=[CH:16][C:17]([C:18]2[N:1]=[C:2]3[N:6]([CH:20]=2)[C:5]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:4]=2[S:3]3)=[CH:12][CH:13]=1)([O-:24])=[O:23]

Participants

5

Reactant 2

HCID 334622-Amino-6-benzothiazololHCID 668402-Bromo-4'-nitroacetophenone

Product 1

HCID 299332572-(4-Nitrophenyl)imidazo[2,1-b]benzothiazol-7-ol

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 702EthanolSolvent

Procedure

2-Amino-6-hydroxybenzothiazole, 2-Bromo-4-nitroacetophenone and absolute Ethanol are added together and heated to reflux for approximately 24 hours. Tetrabutylammonium iodide is added and the reaction is refluxed an additional 12 hours. The resulting yellow suspension is cooled and the solids collected and washed with Ethanol and Diethyl ether. The solids are dried under vacuum to give Intermediate 2.

Workup

  1. temperatureheated
  2. temperatureto reflux for approximately 24 hours
  3. temperaturethe reaction is refluxed an additional 12 hours
  4. temperatureThe resulting yellow suspension is cooled
  5. customthe solids collected
  6. washwashed with Ethanol and Diethyl ether
  7. customThe solids are dried under vacuum

Sources & evidence

ORD record
ord-996d97c419bc40769811793a3d83e76c
Source dataset
uspto-grants-2014_11
Patent number
US08883783B2

Reaction notes

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